Intramolecular nitrile oxide-alkene cycloaddition of sugar derivatives with unmasked hydroxyl group(s)

Tony Kung Ming Shing, Wai F. Wong, Hau M. Cheng, Wun S. Kwok, King H. So

Research output: Contribution to journalArticle

39 Citations (Scopus)

Abstract

(Chemical Equation Presented) Intramolecular nitrile oxide-alkene cycloaddition (INOC) of sugar derivatives with one to four free hydroxyl group(s) is reported. The INOC reaction, using chloramine-T, in the presence of silica gel, to generate nitrile oxides from oximes, proceeded smoothly to afford five- or six-membered carbocycles in good to excellent yields. This new methodology alleviates protection/deprotection steps and makes the synthetic route shorter and more efficient.

Original languageEnglish
Pages (from-to)753-756
Number of pages4
JournalOrganic Letters
Volume9
Issue number5
DOIs
Publication statusPublished - 2007 Mar 1
Externally publishedYes

Fingerprint

Nitriles
Cycloaddition
nitriles
Cycloaddition Reaction
cycloaddition
Alkenes
sugars
Sugars
Hydroxyl Radical
Oxides
alkenes
Derivatives
oxides
Oximes
Silica Gel
silica gel
routes
methodology

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Intramolecular nitrile oxide-alkene cycloaddition of sugar derivatives with unmasked hydroxyl group(s). / Shing, Tony Kung Ming; Wong, Wai F.; Cheng, Hau M.; Kwok, Wun S.; So, King H.

In: Organic Letters, Vol. 9, No. 5, 01.03.2007, p. 753-756.

Research output: Contribution to journalArticle

Shing, Tony Kung Ming ; Wong, Wai F. ; Cheng, Hau M. ; Kwok, Wun S. ; So, King H. / Intramolecular nitrile oxide-alkene cycloaddition of sugar derivatives with unmasked hydroxyl group(s). In: Organic Letters. 2007 ; Vol. 9, No. 5. pp. 753-756.
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